5128-69-8

Upstream product

• 50-00-0 formaldehyd 
• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 
• 6133-29-5 7-methoxy-4-oxo-chroman-3-carbaldehyde 
• 3049-07-8 pentaphenylbismuth 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 47252-14-2 triphenylbismuth carbonate 
• 75-11-6 diiodomethane 
• 92714-96-0 α-chloromethylbenzyl 2-hydroxy-4-methoxyphenyl ketone 
• 94104-29-7 3-hydroxymethyl-7-methoxy-3-phenyl-2,3-dihydro-4H-1-benzopyran-4-one 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 536-74-3 phenylacetylene 
• 3076-54-8 phenyllead(IV) triacetate 
• 143358-20-7 (R,S)-7-hydroxy-3-phenylchroman-4-one 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1621-56-3 7-methoxyisoflavone 
• 4308-55-8 7-Methoxyisoflavan 
• 88794-86-9 3,4-Dihydro-7-methoxyspiro<2H->-1-benzopyran-4,2'-<1,3>-dithiolan 
• 4281-30-5 cis-7-Methoxy-isoflavan-4β-ol 

Relevant academic research and scientific papers

Enantioselective Synthesis of Isoflavanones by Catalytic Dynamic Kinetic Resolution

A ruthenium-catalyzed asymmetric transfer hydrogenation of racemic isoflavanones with dynamic kinetic resolution yields virtually enantiopure isoflavanols as single diastereomers. Subsequent oxidation gives rise to isoflavanones in high enantiomeric purit

Design and synthesis of ERα/ERβ selective coumarin and chromene derivatives as potential anti-breast cancer and anti-osteoporotic agents

Several new coumarin and chromene prototype derivatives have been synthesised and evaluated for their ERα and ERβ selective activity. Coumarin prototype compounds 18 & 19 were found to be ERα selective and the most active, exhibiting potential antiproliferative activity against both ER +ve & ER -ve breast cancer cell lines. The surprise finding of the series, however, are the novel prototype III chromenes 45 & 46, with aroyl substitution at the 6th position. Both the compounds have shown potent antiproliferative activity against both the breast cancer cell lines, promote alkaline phosphatase activity, enhance osteoblast mineralization in vitro, significantly decrease ERE-ERα dependent transactivation and induce ERβ activity. This specific upregulation of ERβ isoform activity of compound 45 may be responsible for the antiosteoporotic activity at picomolar concentration. In addition, both the compounds were also devoid of any estrogenic activity, which correlates to their antiestrogenic behaviour in the two breast cancer cell lines. Assessment of selectivity using specific SiRNAs for ERα and ERβ revealed that most of the compounds showed ERα and ERβ-mediated action, except compound 28, which showed selectivity to ERα only. Computational docking analysis of active compounds 18 and 45 was conducted to correlate the interaction with the two receptors and it was found that the docked conformations of the coumarin prototype, compound 18 at ERα and ERβ active sites were more or less superimposable on each other. However, the unique orientation of the aminoalkoxy side chain of novel chromene (prototype III) compound 45 in the ERβ binding cavity may be responsible for its potential biological response. The Royal Society of Chemistry.

Development of a new class of aromatase inhibitors: Design, synthesis and inhibitory activity of 3-phenylchroman-4-one (isoflavanone) derivatives

Aromatase (CYP19) catalyzes the aromatization reaction of androgen substrates to estrogens, the last and rate-limiting step in estrogen biosynthesis. Inhibition of aromatase is a new and promising approach to treat hormone-dependent breast cancer. We present here the design and development of isoflavanone derivatives as potential aromatase inhibitors. Structural modifications were performed on the A and B rings of isoflavanones via microwave-assisted, gold-catalyzed annulation reactions of hydroxyaldehydes and alkynes. The in vitro aromatase inhibition of these compounds was determined by fluorescence-based assays utilizing recombinant human aromatase (baculovirus/insect cell-expressed). The compounds 3-(4-phenoxyphenyl)chroman-4- one (1h), 6-methoxy-3-phenylchroman-4-one (2a) and 3-(pyridin-3-yl)chroman-4-one (3b) exhibited potent inhibitory effects against aromatase with IC50 values of 2.4 μM, 0.26 μM and 5.8 μM, respectively. Docking simulations were employed to investigate crucial enzyme/inhibitor interactions such as hydrophobic interactions, hydrogen bonding and heme iron coordination. This report provides useful information on aromatase inhibition and serves as a starting point for the development of new flavonoid aromatase inhibitors.

Formation of hydridocobalt(iii) phthalocyanine by reaction of cobalt(ii) phthalocyanines with sodium borohydride and its reactions with antioxidant isoflavones

The reduction of substituted isoflavones with sodium borohydride catalyzed by cobalt(ii) phthalocyanines has been achieved efficiently to yield cis- and trans-isoflavan-4-ols under mild conditions via the formation of a hydridocobalt(iii) phthalocyanine i

Synthesis, anticancer and antioxidant activities of 7-methoxyisoflavanone and 2,3-diarylchromanones

A convenient, fast and high yielding method for the preparation of 7-methoxyisoflavanone and 2,3-diarylchromanones has been developed by the condensation of benzyl-2-hydroxy-4-alkoxyphenylketone with arylaldehyde/paraformaldehyde in presence of diethylamine, assisted by microwave activation. All the synthesized compounds were screened for anticancer as well as antioxidant activities. Among the nine compounds, 7-methoxyisoflavanone 7 and diarylchromanone 6c shows potential anticancer activity and diarylchromanone 6b has potential antioxidant activity. Compound 6h possesses anticancer and antioxidant activity at the same concentration.

Gold(I)-catalyzed annulation of salicylaldehydes and aryl acetylenes as an expedient route to isoflavanones

(Chemical Equation Presented) The value of gold 'n' rings: An isoflavanone moiety is the key structural feature of many complex natural products. It is now shown that such structures can be generated efficiently and atom economically by the annulation of

Organolead-mediated Arylation of Allyl β-Ketoesters: A Selective Synthesis of Isoflavanones and Isoflavones

Arylation of A-ring substituted and unsabstituted 3-allyloxycarbonylchroman-4-ones with aryllead(IV) triacetates followed by selective catalytic deallyloxycarbonylation affords isoflavanones or isoflavones in high overall yields.The highest yield in the arylation step was observed in the reaction of 5,7-dimethoxychroman-4-one with the more hindered 2,4,6-trimethoxyphenyllead triacetate.

Some novel observations on ethoxymethylation of 2-hydroxy- and 2-methoxyphenyl benzyl ketones: Isolation of α-methylene- and α-hydroxymethyl derivatives

Ethoxymethylation of benzyl 2-hydroxyphenyl ketones (6a, 6b and 6c) with two mol equivalents of ethoxymethyl chloride in the presence of K2CO3 and DMF affords directly the isoflavanones (8a, 8b, and 8c respectively) albeit in smaller yields than recorded earlier .In the case of 6a and 6b, α-methylene derivatives (7a and 9) are also formed.However, ethoxymethylation of benzyl-2-methoxyphenyl ketones (10a, 10b and 10c) with one mol equivalent of ethoxymethyl chloride under similar conditions gives invariably the α-methylene derivatives (11a, 11b and 11c respectively) and α-hydroxymethyl derivative (12).

A New General Synthesis of Hydroxy- and Methoxy-isoflavones

A new general synthesis of hydroxy- (5e-h) and methoxy- (5e-d) isoflavones has been accomplished in overall yields of 47-73percent from the corresponding 2-hydroxydeoxybenzoins (1a-h).The first step involves reaction with appropriate amounts of ethoxymeth